The present invention relates to 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers defined according to the structure: ##STR5## wherein R' represents methyl or ethyl and wherein R.sub.1 and R.sub.2 taken alone are the same or different hydrogen, phenyl, C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) and R.sub.1 and R.sub.2 taken together represent C.sub.5 -C.sub.12 cycloalkyl or alkyl cycloalkyl, and reaction products containing same as well as uses thereof in order to alter, modify or enhance the aroma of consumable materials.
There has been considerable work performed relating to substances which can be used to impart (alter, modify or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials some of which may be in short supply and to provide more uniform properties in the finished product.
Green, herbaceous, basil, parsley, rose, fruity, mandarin orange peel, spicy, earthy, rooty, sauge sclaree, minty, woody, celery-like, citrusy, seashore, fresh, clean, ozoney, tangerine-like, grapefruit-like, Nootkatone-like, jasmine, dill, caraway, nutty, coconut, floral, peach-like, apricot-like, caramel-like, maple syrup and new mown hay aromas, with galbanum, jasmine, celery-like, green, pineapple, cinnamon, pineapple, oak moss, almond oil, animalic, herbaceous, camphoraceous and eucalyptus-like topnotes, and fruity, floral, jasmine, lily of the valley, green, herbaceous, animalic, dill, caraway, citrusy, sweet citrus, straw-like and bergamot undertones are highly desirable in several types of perfume compositions, perfumed articles and colognes.
The perfume use of 2,4-disubstituted tetrahydropyranols having the structures: ##STR6## is disclosed in the literature as follows:
(a) the perfume use of the compound having the structure: ##STR7## USSR Patent 620487 of July 17, 1978 (Chemical Abstracts 89: 185929p);
(b) the compound having the structure: ##STR8## USSR Patent 638597 of Dec. 28, 1978 (Chemical Abstracts, Volume 90: 109812a);
(c) the compound having the structure: ##STR9## USSR Patent 618374 of Aug. 5, 1978 (Chemical Abstracts 89: 179861u).
The perfumery uses of compounds defined according to the generic structure: ##STR10## wherein R.sub.1 ' and R.sub.2 ' are defined, supra, including compounds of the subgenuses: ##STR11## is well known in the prior art. Thus, for example, U.S. Letters Patent 3,681,263 (Van der Linde, et al) discloses the use of the compounds having the structures: ##STR12## in perfumery (mixtures wherein in the mixtures in each of the compounds one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds) using as an intermediate to form such compounds the compound having the structure: ##STR13## Van der Linde, et al also discloses the perfumery use of the compound having the structure: ##STR14## and the synthesis process, to wit: ##STR15##
Hall, et al, U.S. Letters Patent 4,240,447 discloses the genus of compounds defined according to the structure: ##STR16## for use in perfumery wherein the moieties R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 may be hydrogen or alkyl and one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines are carbon-carbon single bonds in each of the compounds disclosed.
Netherlands Published Patent Application 68/08496 discloses the genus of compounds defined according to the structure: ##STR17## wherein A completes a cycloalkyl moiety and the moieties R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13 and R.sub.14 represent hydrogen or alkyl . . . including the compound having the structure: ##STR18## (formula 15).
Vinals, et al, U.S. Letters Patent 4,070,491, at columns 15 and 16, discloses the organoleptic uses of the compound having the structure: ##STR19## wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.
Nothing in the prior art discloses the 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers of our invention for their organoleptic utilities.
In addition, the prior art discloses synthetic routes to the genus of compounds having the structure: ##STR20## to wit: Chem. Abstracts Volume 101: 54857g disclosing the genus of compounds having the structure: ##STR21## wherein R.sub.3 and R.sub.4 represent alkyl, hydrogen, phenyl, vinyl, cyclohexyl and cyclopentyl; Chem. Abstracts Volume 87: 5757h disclosing the synthesis route: ##STR22## Chem. Abstracts Volume 101: 54857 disclosing the synthesis route: ##STR23## Chem. Abstracts Volume 94: 47139h disclosing the synthesis route: ##STR24##
Nothing in the prior art shows synthesis routes which will effect production of the 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers of our invention.